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A π-acid tetracyanoethylene (TCNE) and its derivative dicyanoketene dimethyl acetal (DCKDMA) were found to catalyze esterification of lauric acid with various types of alcohols. This mathod was successfully applied to methyl esterification of a variety of carboxylic acids including aromatic, α,β-unsaturated, α-hydroxy, and N-Cbz and N-Boc-protected α-amino acids without racemization at the range from room temperature to 60 °C. TCNE was also found to operate as a catalyst in transesterification reaction of methyl laurate.
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Masaki et al. (1997) studied this question.
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